The objectives of the research are as follows: (1) Development of a total synthesis of Cerulenin which is sufficiently practical to provide a synthetic source of this material and at the same time a final confirmation of the structure. (2) Preparation of analogs and homologs as appropriate, to establish a structure activity correlation. (3) Confirmation or revision of the proposed structure for the medium ring lactonic antibiotic Vermiculine. (4) Total synthesis of Vermiculine once the correct structure has been established. (5) Production of synthetic derivatives which may possess interesting biological activity. We will explore simultaneously three independent routes to the proposed structure for Cerulenin. The utility of an internal Darzans reaction will be explored, which may result in a general synthesis of B epoxy butenbutenolides. The key precursors will be epoxy lactones or anhydrides since the corresponding double bond compounds are either not useful or configurationally unstable. A sample of Vermiculine will be degraded via zinc reduction to a diketo carboxylic acid. A comparison will then be made with the authentic independently prepared sample. The structure if incorrect will be suitably revised. A total synthesis of Vermiculine will then be undertaken to confirm the structure. A proposed route involves forming the desired nine membered lactione via coupling an appropriate bis allylic halide. With a sufficient supply of Vermiculine in hand, epoxidation among other derivations will be utilized to prepare a compound which is closely related to Cerulenin and may possess potent biological activity.